Ben Whittaker (Robert DeNiro) is a retired widower who feels he's already made the most of his free time. Without his wife, many activities lack the appeal they once had, and after a point, even the ones you enjoy by yourself lose their luster. Seeking structure, Ben visits his neighborhood Starbucks bright and early each morning and generally tries to keep up some semblance of routine. It makes sense, then, that he perks at the opportunity to work as a senior intern. He's smart, curious, and bored. What could be better?
To be honest, it would probably be a lot better if Type-A overachiever Jules Ostin (Anne Hathaway) had any memory of agreeing to the project or any idea why it was happening. Wouldn't the point be to get in touch with an older demographic? Maybe learn about them as potential customers and mine their experience for business tips? Instead, Jules rolls her eyes at the whole thing and leaves her senior citizen interns fetching coffee alongside her senior-in-college interns, a colossal waste of everyone's time.
As Ben settles into office culture, establishing connections with everyone in the department, he gradually moves into Jules' inner circle. His arrival happens to coincide with the news that "they" want Jules to look for a CEO for her company, a soul-crushing revelation for a girl who has built the business from the ground up and oversees every aspect of its operation. It's never made clear who "they" are, since Jules very obviously runs the company, but there is a voice inside the phone who tells her what to do and makes her cry.
While Jules searches for the person who will make her redundant, she finds Ben an unexpectedly reliable and surprisingly insightful ally. Not only does he have a practical, no-nonsense approach to getting things done, he serves as a thoughtful and sympathetic sounding board. Though Jules is dismissive at first, she soon realizes that Ben is exactly the dose of reality she needs. After pouring so much energy into work, Jules' marriage has hit a rocky patch, she doesn't fit in with the moms at her daughter's school, and she has a fraught relationship with her own mother. Basically she needs a friend.
The fact that Ben fills this role is as endearing as it is entertaining. As Jules' navigates this turning point in her life, her intern essentially becomes a mentor. In turn, Ben finds himself embraced by a whole new set of friends, and even begins a romance with the office masseuse (Rene Russo). The moral is perhaps that reaching outside one's personal bubble leads to great rewards. It's a sentiment that gives us reason enough to overlook the movie's flaws.
The DVD + Blu-ray + Digital HD combo edition includes the featurettes "Learning from Experience" (a discussion of the generation gap with the cast and Nancy Meyers), "Designs on Life" (a look at the film's fashion and interior design), and "The Three Interns" (an interview with Adam Devine, Zack Pearlman, and Jason Orley).